In this segment, Usher Raymond and Rebecca Romijn hang out on the roof of the Chateau Marmont to talk about what he wears to feel sexy. He is all of 19 years old, and the two flirt outrageously as he changes clothes three times. For those even slightly less obsessed with Usher than I am, this was a crazy time for the Dallas, Texas -born performer, it's right on the heels of the monstrous success of his 1997 sophomore release My Way. If you don't know, that was the album where Jermaine Dupri and Usher got together and started making warlock music that would destroy the Billboard charts for the next majillion years. It was also the year Usher debuted his acting chops in that Robert Rodriguez movie The Faculty, which starred everyone from Elijah Wood to Salma Hayek and Jon Stewart.

We first see Usher in a bright yellow sweatsuit unzipped to the navel; Clarks Wallies; shades; and diamonds. The suit is from Shabazz Brothers, the line created by the dude Big Daddy Kane would routinely shout out. This was the heyday of urban streetwear like Karl Kani, Phat Farm, Walker Wear by April Walker, Mecca, Maurice Malone, Pure Playaz and Enyce, and Usher’s warm-ups are emblematic of the aesthetic as it existed before sportswear focused on preppier, collegiate elements, and the “grown and sexy” vibe that you see in his video for the single “You Remind Me.” (That's the one where Usher wears massive, French cuff striped button-down shirts, sateen shirts and summer-weight suits so baggy they look like pajamas.)

Next is a short-sleeved, white logo button-down from Phat Farm, worn with a cotton tank and chinos. A do-rag and Cartier sunglasses finish off the look. What follows is the final ensemble: yet another Phat Farm top — this time a pique polo with an embroidered back — and baggy shorts. It’s notable that while Usher’s clothes became more fitted over the years, the general idea remains the same: a heavy reliance on dark tees, jeans and button downs.

STREET STYLE: JAMES KING ON WHO'S "THE BOMB"

Model James King finds out what's sexy on the streets of New York in 1998.Photo: MTV

That she had a boy’s name and was regularly seen on the downtown New York scene made James King (now Jamie) undeniably cool. She has an insouciance about her and even when designers put her in the skimpiest outfits, she always looked badass and confident. It's what makes her perfect for walking around NYC to decide who’s cool. This is 1998, mind you, so, hilariously enough, she’s actually going around deciding who’s “The Bomb” (cue Funkmaster Flex explosion sounds). LOLOLOLOLOL.

James is a master at plucking out bomb people. Her hair is loose, she’s barely wearing any makeup, and she’s in a black tank and boot-cut jeans that are split up the front to create the illusion of unzipped basketball track pants. It’s a particularly ’90s way of distressing jeans that you never see anymore but should.

James runs up on a guy and calls him over for being “sexy.” He’s wearing a massive Knicks starter jacket, loose jeans and a necklace. They talk a little about what they each find attractive, and she calls him out for dripping with good energy. They’re visibly taken with each other, but observe one other analytically. It’s like watching two cool people smell each other’s butts. Then the dude’s friend —who I swear is a young Amy Gunther in cornrows (that’s the model who started the iconic skate shop KCDC) — saunters over looking angelic in a white tank and simple skirt.

Next it’s off to the park, where we see a cute girl who epitomizes 1998 summer style in skintight pedal pushers, platform flip-flops and a head scarf. Then there’s another grouping of kids in summer dresses and tees. We even talk briefly to a dude in a ringer T-shirt and Air Maxes who attempts to holler at James. It’s hilarious how quickly she deflects him while addressing us about how easy it is for guys to be “The Bomb,” since so much of it relies on their attitude. It’s sorta like a Richard Attenborough voiceover on a nature show, and it’s great.

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